MONOFLUORO ANALOGS OF EUGENOL METHYL-ETHER AS NOVEL ATTRACTANTS FOR THE ORIENTAL FRUIT-FLY

Monofluoro analogs of eugenol methyl ether as potential attractants for the Oriental fruit fly (Bactrocera dorsalis, Hendel) were synthesized using selective fluorination reactions: electrophilic hydro- and iodofluorination, fluorodehydroxylation with (diethylamido)sulfur trifluoride (DAST), and Wittig fluoroolefination through the stabilized ylides. Unusual reduction of the double bond was detected in a reaction of eugenol methyl ether with pyridinium poly(hydrogen fluoride). Bis-[(3,4-dimethoxyphenyl)alkyl] carbonates were identified as the novel nucleophilic substitution products of the intermediate generated from the reaction of 3,4-dimethoxybenzenealkanols with DAST. Reductive desulfonylation of fluorovinyl sulfone 24-(Z) with sodium amalgam afforded 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene (E/Z = 85:15) which was highly attractive to the Oriental fruit fly.